Carboxylative cyclization of propargylic amines with CO2 catalyzed by dendritic N-heterocyclic carbene-gold(I) complexes

被引：45

作者：

Fujita, Ken-ichi ^{[1
]}

Inoue, Kensuke ^{[2
]}

Sato, Junichi ^{[3
]}

Tsuchimoto, Teruhisa ^{[2
]}

Yasuda, Hiroyuki ^{[1
,3
]}

机构：

[1] Natl Inst Adv Ind Sci & Technol, Tsukuba Cent 5,1-1-1 Higashi, Tsukuba, Ibaraki 3058565, Japan

[2] Meiji Univ, Dept Appl Chem Sch Sci & Technol, Tama Ku, Kanagawa 2148571, Japan

[3] Ibaraki Univ, Grad Sch Sci & Engn, 2-1-1 Bunkyo, Ibaraki 3108512, Japan

来源：

TETRAHEDRON | 2016年 / 72卷 / 09期

关键词：

NHC-gold(I) complex; Carbon dioxide; Propargylic amine; 2-Oxazolidinone; MIYAURA COUPLING REACTION; ARYL ETHER DENDRIMERS; CARBON-DIOXIDE; CHEMICAL-YIELD; AQUEOUS-MEDIA; DIELS-ALDER; OXAZOLIDINONES; LIGANDS; FIXATION; BEARING;

D O I：

10.1016/j.tet.2016.01.016

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We prepared several of a new type of dendritic N-heterocyclic carbene (NHC)-gold(I) complex. In particular, by employing an amphiphilic dendritic NHC-gold(I) complex having penta(ethylene glycol) units at the peripheral layer as a catalyst, the aqueous media carboxylative cyclization of propargylic amines proceeded smoothly to provide the corresponding 2-oxazolidinone at room temperature under atmospheric pressure of CO2. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：1205 / 1212

页数：8

共 44 条

[1]

[Anonymous], 2001, Wiley-VCH Verlag GmbH Co. KGaA

[2]

Bailey F.E., 1976, POLYETHYLENE OXIDE

[3] SMART LIGANDS THAT REGULATE HOMOGENEOUSLY CATALYZED-REACTIONS [J].

BERGBREITER, DE ;

ZHANG, L ;

MARIAGNANAM, VM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (20) :9295-9296

[4] Phthalocyanine-centred and naphthalocyanine-centred aryl ether dendrimers with oligo(ethyleneoxy) surface groups [J].

Brewis, M ;

Helliwell, M ;

McKeown, NB .

TETRAHEDRON, 2003, 59 (22) :3863-3872

[5] Where organometallics and dendrimers merge: the incorporation of organometallic species into dendritic molecules [J].

Chase, PA ;

Gebbink, RJMK ;

van Koten, G .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (24) :4016-4054

[6]

Clinton N., ENCY POLYM SCI ENG, V6, P225

[7]

Cong L.-Z., 2001, TETRAHEDRON LETT, V42, P7337

[8] Electrochemically promoted C-N bond formation from acetylenic amines and CO2.: Synthesis of 5-methylene-1,3-oxazolidin-2-ones [J].

Feroci, M ;

Orsini, M ;

Sotgiu, G ;

Rossi, L ;

Inesi, A .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (19) :7795-7798

[9]

Frechet J. M. J., 2001, DENDRIMERS OTHER DEN

[10] Dendrimer N-heterocyclic carbene complexes with rhodium(I) at the core [J].

Fujihara, T ;

Obora, Y ;

Tokunaga, M ;

Sato, H ;

Tsuji, Y .

CHEMICAL COMMUNICATIONS, 2005, (36) :4526-4528

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